


I Really Shouldn't

by Kaepore



Category: Original Work
Genre: Biting, Blood, F/M, Pegging, Sexual Roleplay
Language: English
Status: Completed
Published: 2019-07-20
Updated: 2019-07-20
Packaged: 2020-07-09 02:56:28
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,442
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19880461
Author URL: https://archiveofourown.org/users/Kaepore/pseuds/Kaepore
Summary: Fucking your boyfriend's roommate shouldn't be this fun.





	I Really Shouldn't

**Author's Note:**

> I procrastinated on this for MONTHS. I finally got it done. Please enjoy. :)

“Hey, Karter I went by that place...” Wesley stops in his tracks, staring wide-eyed at his roommate’s girlfriend, Sam.

Sam sits perched on the edge of Karter’s dorm room bed, a strapon clinging to her jean covered hips. The lube covering the shaft glistens under the light, catching Wesley’s eye.

Sam stares, her eyes wide. She quickly recovers from the shock and gives Wesley a sly smile. “I wasn’t expecting you to be here.” She comments.

Wesley blushes, looking away and shuffling from foot to foot. “Well, uh. This is my dorm room as well,” He answers, gesturing to his bed on the other side of the room.

“Indeed it is. I just meant that Karter said you weren’t going to be home anytime soon is all.”

Wesley nods and looks at her, “What uh, were you guys going to do?”

“Well, If you would love to know, I was going to fuck Karter into this mattress but,” Sam trails off, motioning towards him.

“Oh Uh well, I could uh,” Wesley tries to grasp for the right words but can’t seem to do so.

Sam gracefully slides off the bed, moving towards Wesley. She looks up at him, a playful smile dances on her lips as she traces a finger down his chest.

“Yeah?” She says, encouraging him on.

Wesley’s mind is running as he thinks of what to say. His eyes drift down to the strapon that is still around Sam’s waist.

Sam smirks at him as she follows his gaze. “You want a taste?”

Wesley nods and Sam grabs his hand, leading him to the bed. She pushes him to his knees and leans him back against the edge of the bed.

“Can you deep throat?” Wesley nods in response and Sam smiles.

“Good. So, while we do this, keep your hand on my thigh. Tap me if you want to slow down, and squeeze if you want me to stop. I don’t want to push you any further than you want to.” Sam explains, carding her fingers through Wesley’s hair as she explains.

Wesley nods and leans into her hand. Sam grabs a fist full of his hair. “You can snuggle my hand later. Open up,” she commands.

Wesley parts his lips wide enough for the strapon to slide in. He slacks his jaw to make himself more comfortable when his teeth scrape the silicone. He looks up into Sam’s eyes, his stomach flutters. Blood rushes to his dick and Sam takes notice.

She grabs the back of Wesley’s head and pushes the strapon down his throat. Wesley gags around the silicone and Sam moans at the sound. She pulls the strapon out halfway, but Wesley hooks his fingers into her belt loops and pulls her hips back in.

Sam slips her fingers through his hair and grabs a fistful. “Relax your throat and jaw,” She warns him. He nods and does as he’s told. She slowly pulls out of his mouth and forcefully thrusts back in.

Wesley gags even worse than before. Sam waits for any signal to slow down or stop, but Wesley just looks up at her, a needy look in his eyes. She smirks down at him and thrusts back into his mouth, starting at a slow pace to get him used to the feeling. 

Wesley looks up at her, nodding slightly to let her know that she can continue and speed up. Sam grabs a fistful of his hair and leans him back against the bed. She angles her hips to where she can get a steady rhythm and to put him in the least amount of pain.

Sam leans a hand on the mattress and keeps the other in Welseys hair as she thrusts unforgivingly into his mouth. Wesley whimpers and snakes an arm around Sam’s waist, and his hand up her shirt. 

“Fuck, Wes,” Sam moans out, pulling his head closer. Wesley responds by sliding his hand further up her shirt, cupping one of her breasts. She moves her leg between Wesley’s, pressing against his erection. The pressure causes him to buck against her, causing him to let out a long groan through the rapid and now sloppy thrusts. 

Sam suddenly releases the vice-like grip on his hair and steps back from Wesley. He falls forward, gasping for breath. “Are you okay?” Sam asks, kneeling to look at him, lifting his head by his chin.

Wes nods at her and smiles. “Are you ready for more?” She asks, and he nods once more. Sam helps him up from the floor and pushes him down on the bed. She leans down to unbuckle his belt, maintaining eye contact with him as she slides his jeans and boxers off. He slides his shirt off, doing part of the work for her.

She stands and takes a step back from him, admiring the view. "Facedown on the bed. Ass in the air," she commands. Wesley scrambles into position, eager to please her. Sam smiles at how submissive he is. She slowly rakes her fingers through his hair, trailing them down his back and slopes her hand over the curve of his ass.

Wesley shivers under her hand, gasping when her hand slides between his legs, cupping his balls. He spread his legs wider for her, but she pulls away. Sam grabs the small bottle of lube from Karter's nightstand, covering her fingers generously before she moves back between his legs. Wesley gasps at the cold feeling, and a single finger pushing into him. 

Sam leans down, pressing her lips to his shoulder, smiling as he grips the sheets in his fingers. "More, please Sam," he begs. His voice barely above a whisper." She happily complies, adding two more fingers, stretching him wider.

Wes hisses at the slight burn, but moves his hips back, pushing her fingers deeper into him. "Hm. Someone seems eager," Sam teases as she presses her fingers deeper, barely ghosting over his prostate. Wesley groans softly, cheeks flushing. He slowly slides his hands down his hips, fingers closing over his dick.

Sam grips his hair, pulling his head back at a painful angle to whisper in his ear, "Touch yourself, and I'll stop. You want to be a good boy for me, don't you?" 

Wesley nods frantically, "Yes, yes. I'm sorry. Please don't stop!" He begs, desperately rutting against the sheets, trying to gain as much pleasure as he can. He whines when Sam lets go of his hair and moans when she slips her fingers out of him. 

Sam kneels onto the bed between his legs and grabs his ass, admiring the way the flesh bulges between her fingers. She lets one cheek go and lands a sharp slap. Wesley jerks and whimpers at the sting. Sam leans over, grabbing the lube again and adding more to the strapon.

She gets down behind Wesley, pressing the silicon head against his hole. He pushes back against her, pushing the head in. He squirms slightly, making Sam push his hips down against the mattress. 

Sam thrusts lightly, getting him used to the feeling before she grabs his hair and pins his wrists against his back and slams into his hole. Wesley lets out a strangled cry, losing the ability to form words.

"Plea.. se, I ne... ed it, fuck me hard." He fumbles over his words at Sam pushed against his prostate, hips speeding up as he speaks. 

"Are you sure baby boy?" She inquires, "I don't want to push you further than you can go."

"Please, please, more. I can handle it!" He begs, jaw going slack in the progress. She keeps up the pushing pace against his prostate, leaning down and sinking her teeth into his shoulder. 

Wesley gasps, "Harder, bite me harder. I want you to draw blood." She flips him around, laying him on his back. He muffles a whimper when she sinks back into his tight heat. His legs wrap around her hips, meeting the thrusts. She sinks her teeth in the same spot, only stopping when she tastes copper.

Wesley is shaking as he grips Sam's shirt for dear life. She bites down in several more places, drawing blood each time. Wesley's nails dig into her back, his hole clamps down and flutters against the silicone as he cries out, cumming all over himself. "Fuck, Sam!"

Sam slows her thrusts, riding out his orgasm. When she pulls out, she rolls over next to Wesley. She smiles at him, "How was that baby?"

Wesley gasps for breath as he nods, "I loved it."

"Yeah, and you thought roleplay would be stupid." She teases, leaning over to kiss him.

**Author's Note:**

> Please tell me if there are any mistakes you caught, or have any questions! :)
> 
> You can find this on my Tumblr:
> 
> https://kaepore.tumblr.com/post/186415616472/i-really-shouldnt


End file.
